Novel generation of 3,3,3-trifluoropropynyllithium and transformation of the carbonyl adducts to trifluoromethyl-substituted allenes

Masaki Shimizu; Masahiro Higashi; Youhei Takeda; Guofang Jiang; Masahito Murai; Tamejiro Hiyama

doi:10.1055/s-2007-977422

Novel generation of 3,3,3-trifluoropropynyllithium and transformation of the carbonyl adducts to trifluoromethyl-substituted allenes

Masaki Shimizu, Masahiro Higashi, Youhei Takeda, Guofang Jiang, Masahito Murai, Tamejiro Hiyama

Research output: Contribution to journal › Article › peer-review

19 Citations (Scopus)

Abstract

A novel method for the generation of 3,3,3-trifluoropropynyllithium is reported, which involves treatment of trifluoromethyl-substituted enol tosylate, prepared from 1,1-dichloro-3,3,3-trifluoroacetone, with two equivalents of butyllithium. Palladium-catalyzed coupling reaction of sulfonates of the carbonyl adducts with organozinc reagents gave trifluoromethyl-containing tri- and tetrasubstituted allenes.

Original language	English
Pages (from-to)	1163-1165
Number of pages	3
Journal	Synlett
Issue number	7
DOIs	https://doi.org/10.1055/s-2007-977422
Publication status	Published - Apr 24 2007
Externally published	Yes

Keywords

Alkynes
Allenes
Fluorine
Lithium
Palladium

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-2007-977422

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abstract = "A novel method for the generation of 3,3,3-trifluoropropynyllithium is reported, which involves treatment of trifluoromethyl-substituted enol tosylate, prepared from 1,1-dichloro-3,3,3-trifluoroacetone, with two equivalents of butyllithium. Palladium-catalyzed coupling reaction of sulfonates of the carbonyl adducts with organozinc reagents gave trifluoromethyl-containing tri- and tetrasubstituted allenes.",

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author = "Masaki Shimizu and Masahiro Higashi and Youhei Takeda and Guofang Jiang and Masahito Murai and Tamejiro Hiyama",

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doi = "10.1055/s-2007-977422",

language = "English",

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T1 - Novel generation of 3,3,3-trifluoropropynyllithium and transformation of the carbonyl adducts to trifluoromethyl-substituted allenes

AU - Shimizu, Masaki

AU - Higashi, Masahiro

AU - Takeda, Youhei

AU - Jiang, Guofang

AU - Murai, Masahito

AU - Hiyama, Tamejiro

PY - 2007/4/24

Y1 - 2007/4/24

N2 - A novel method for the generation of 3,3,3-trifluoropropynyllithium is reported, which involves treatment of trifluoromethyl-substituted enol tosylate, prepared from 1,1-dichloro-3,3,3-trifluoroacetone, with two equivalents of butyllithium. Palladium-catalyzed coupling reaction of sulfonates of the carbonyl adducts with organozinc reagents gave trifluoromethyl-containing tri- and tetrasubstituted allenes.

AB - A novel method for the generation of 3,3,3-trifluoropropynyllithium is reported, which involves treatment of trifluoromethyl-substituted enol tosylate, prepared from 1,1-dichloro-3,3,3-trifluoroacetone, with two equivalents of butyllithium. Palladium-catalyzed coupling reaction of sulfonates of the carbonyl adducts with organozinc reagents gave trifluoromethyl-containing tri- and tetrasubstituted allenes.

KW - Alkynes

KW - Allenes

KW - Fluorine

KW - Lithium

KW - Palladium

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DO - 10.1055/s-2007-977422

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JO - Synlett

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IS - 7

ER -

Novel generation of 3,3,3-trifluoropropynyllithium and transformation of the carbonyl adducts to trifluoromethyl-substituted allenes

Abstract

Keywords

ASJC Scopus subject areas

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